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Can't send text messages to 1 phone number only

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Hey! I have an iphone 5 and have never had a problem sending messages to a person, but I can't send texts to my boyfriend. We both live in Alaska but he has a flip phone and I have a smart phone. My friends can text him and he can text me, but everytime I try sending him a message, it says please enter a valid 10 digit number. I have entered it so many different ways, but nothing has worked. I even sat with AT&T guys at our local store and he couldn't figure it out either. Please help me! It's so frustrating!


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